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Synthesis method of 1,2,3-phentriazine-4(3H)-one compound

A synthetic method and benzotriazine technology, applied in the field of chemistry, can solve the problems of increasing difficulty, long reaction cycle, cumbersome operation procedures, etc., and achieve the effects of easy acquisition, easy post-processing, and simple experimental operation

Inactive Publication Date: 2018-05-29
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, the currently used diazotization reaction involves the starting materials being carried out under acidic conditions, which makes it difficult to tolerate acid-sensitive functional groups, and the step-by-step strategy makes the reaction period long and the operation procedures cumbersome, thereby improving the industrial production of the reaction. difficulty

Method used

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  • Synthesis method of 1,2,3-phentriazine-4(3H)-one compound
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  • Synthesis method of 1,2,3-phentriazine-4(3H)-one compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Synthesis of 1,2,3-benzotriazin-4(3H)-one:

[0035]

[0036] At room temperature (25°C), 2-aminobenzamide (0.3mmol, 1equiv) and tertbutyl nitrite (0.45mmol, 1.5equiv) were added to the reaction tube, and then the reaction solvent acetonitrile (CH 3 CN) 2mL, the reaction tube was stirred at room temperature, and the reaction process was monitored by thin-layer chromatography. After the reaction was completed in about 3 minutes, 10mL of ethyl acetate was added to dilute, and then the diluted solution was transferred to a separatory funnel and washed with saturated saline Extract, separate the aqueous phase and the organic phase, then use ethyl acetate to extract the aqueous phase 3 times, then combine all the organic phases, then add anhydrous sodium sulfate 5g to dry, filter after 5min, and the filter cake is washed with ethyl acetate (5mL × 3 times), the filtrate was combined, and then the filtrate was concentrated under reduced pressure to spin off the solvent, and ...

Embodiment 2

[0045] Synthesis of 7-chloro-1H-1,2,3-benzotriazin-4-one:

[0046]

[0047] At room temperature (25°C), 2-amino-4-chlorobenzamide (0.3mmol, 1equiv) and tertbutyl nitrite (0.45mmol, 1.5equiv) were added to the reaction tube, and then the reaction solvent CH 3 CN 2mL, stir the reaction tube at room temperature, monitor the reaction process by thin-layer chromatography, the reaction is completed in about 3 minutes, add 10mL of ethyl acetate to dilute, then transfer the diluted solution to a separatory funnel, and extract with saturated saline , separate the water phase and the organic phase, and then extract the water phase with ethyl acetate for 3 times, then combine all the organic phases, then add 5 g of anhydrous sodium sulfate to dry, filter after 5 min, and the filter cake is washed with ethyl acetate (5 mL× 3 times), the filtrate was combined, and then the filtrate was concentrated under reduced pressure to spin off the solvent, and the concentrate was separated by colu...

Embodiment 3

[0056] Synthesis of 8-bromo-1H-1,2,3-benzotriazin-4-one:

[0057]

[0058] At room temperature (25°C), 2-amino-3-bromobenzamide (0.3mmol, 1equiv) and tertbutyl nitrite (0.45mmol, 1.5equiv) were added to the reaction tube, and then the reaction solvent CH 3 CN 2mL, stir the reaction tube at room temperature, monitor the reaction process by thin-layer chromatography, the reaction is completed in about 3 minutes, add 10mL of ethyl acetate to dilute, then transfer the diluted solution to a separatory funnel, and extract with saturated saline , separate the water phase and the organic phase, and then extract the water phase with ethyl acetate for 3 times, then combine all the organic phases, then add 5 g of anhydrous sodium sulfate to dry, filter after 5 min, and the filter cake is washed with ethyl acetate (5 mL× 3 times), the filtrate was combined, and then the filtrate was concentrated under reduced pressure to spin off the solvent, and the concentrate was separated by column...

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Abstract

The invention discloses a synthesis method of a 1,2,3-phentriazine-4(3H)-one compound. 2-aminobenzamide and are used as raw materials and tert-butyl nitrite stirred at the room temperature in a reaction solvent, and the 1,2,3-phentriazine-4(3H)-one compound is obtained through an intramolecular diazotization reaction. The reaction equation is shown in the description, wherein R is H, fluorine, chlorine, bromine, trifluoromethyl, nitryl or methyl. The synthesis method has the benefits as follows: (1) the synthesis method is convenient in experiment operation, easy in posttreatment, mild in reaction condition and suitable of large-scale industrial production; (2) reaction substrate functional groups have high tolerance, and the substrate is wide in range and easy to obtain; (3) the reactionefficiency, yield and purity are higher.

Description

technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing 1,2,3-benzotriazin-4(3H)-one compounds, and belongs to the technical field of chemistry. Background technique [0002] 1,2,3-Benzotriazin-4(3H)-one is a kind of nitrogen-containing heterocyclic compound, which has biological activities such as sterilization, anti-inflammation and inhibition of disordered growth of viruses, so it is widely used as an intermediate in organic synthesis , dyes, preservatives, and are often found in the dominant structure of kinase inhibitors, especially in the field of medicinal chemistry, in order to improve or change the pharmacological activity, often introduce 1,2,3-tri Azole, for example: 1-hydroxy-1, 2, 3-benzotriazin-4(3H)-one is a kind of efficient polypeptide condensation agent. [0003] Current bibliographical reports synthesize 1,2, the method for 3-benzotriazine-4 (3H)-ketone compound mainly is to u...

Claims

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Application Information

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IPC IPC(8): C07D253/08
CPCC07D253/08
Inventor 安翠吴华悦张鑫杨烨翡徐雨婷毕康刘妙昌黄小波高文霞
Owner WENZHOU UNIVERSITY
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